Karen Darrin

Good questions are the foundation of effective career discussions. They can help you better understand your employees, demonstrate your genuine interest in their professional development and create a healthy dialogue about how they can move forward in their careers. Here is a sampling of 10 career development questions you can pick from to get the conversation started.

Meet at least every six months with your employee to discuss their career development. Ahead of the meeting, provide your selected questions to discuss. This gives the employee time to reflect and prepare.

  1. What activities in your job have you enjoyed the most and found most interesting? Which have you disliked? Don’t underestimate the power of simply enjoying the tasks you and your employees do at work each day. For everyone who hates doing accounting, there’s someone who loves it. And these answers may evolve as an employee learns more and tries new activities. It’s important to check in from time to time and reiterate your interest in giving employees, as much as is possible, work they genuinely enjoy.
  2. Which projects from the past year are you most proud of? This question lets your employee use real-life experiences as a means of showing accomplishments. It’s also time-bound so their answers won’t get repetitive and stale.
  3. What are your most valuable talents and skills? This question lets you see how an employee views themselves and their contributions, which may differ from what you assume. It also gives you a chance to offer your observations about their strengths, and how they contribute to the company’s success.
  4. What are your career goals for the next 6 months; year or two? What about 5 years from now? Here you want to understand what your employee wants for their career in specific short- and long-term time frames, and what they’ve done or plan to do about those goals.
  5. What are you already doing to reach those short- and long-term goals? This lets you see what the employee has done already that you might not be aware of, and also to see what they’re planning to do, hoping to do and how you might help.
  6. What projects, committees or other responsibilities would you like to be a part of to help develop your career? Is there another department you’d like to learn more about? If the employee is not sure, you can make suggestions. If you agree on any, this will help their development and possibly your bench depth in other areas.
  7. Would you like a mentor? Is there anyone in the company that you feel would be a good mentor? If not, can I recommend someone? This allows you, as the employer, to see that your employee receives guidance from people you trust to give good advice. It can also develop a third person if the mentor is someone within your company.
  8. Which development activity can you start on now that would be most beneficial to achieving your short-term goals? Your long-term goals? This lets the employees think of concrete actions to begin immediately that will benefit their career. They will likely ask to be introduced to the mentor you suggested earlier, to take a class or to be given higher-level assignments. Listen with an open mind and be ready to accept their ideas or guide them to new ones.
  9. What can I do to help you get started? You can reiterate your interest in being a resource here and in removing obstacles.
  10. Can you report back with your progress in three to six months? This shows your desire for this to be a continuing discussion, not a one-off conversation, and signals to employees that they’ll be held accountable for their results.

Centering each development discussion around the employee’s unique personal goals and experiences, tying them to the organization as a whole and then carrying them forward will show employees that you are serious about their long-term success. They’ll feel more empowered and more valued at your organization. This will benefit the individual and the organization. Development is a win for everyone. Start having discussions today.

Want tips on how to facilitate a career discussion with YOUR boss?  Click here!


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